Herbicide

ABSTRACT

Herbicidal composition of a benzothiadiazinone dioxide derivative and a urea derivative.

Umted States Patent [191 [111 3,912,489 Fischer 1 Oct. 14, 1975 HERBICIDE [58] Field of Search 71/91, 120 [75] Inventor: Adolf Fischer, Mutterstadt,

Germany [56] References Cited 73 Assignee: Badische Anilin- & Soda-Fabrik UNITED STATES PATENTS Aktiengesenschaft, Ludwigshafen 3,149,955 9/1964 Fischer et al. 71/120 (Rhine) Germany 3,708,277 l/1973 Zeidler et a]. 71/91 Filed: June 1972 Primary Examiner-Elbert L. Roberts [21] AppL No; 258,711 Assistant Examiner-Catherine L. Mills Attorney, Agent, or FirmJohnston, Keil, Thompson & Shurtleff [30] Foreign Application Priority Data June 24, 1971 Germany 2131401 [57] ABSTRACT Herbicidal composition of a benzothiadiazinone diox- [52] US. Cl. 71/91; 71/90; 71/99;

7 H lde derivative and a urea derivatlve. [51] Int. Cl. A01N 9/22 1 Claim, No Drawings HERBICIDE The present invention relates to a herbicide comprising a composition of a benzothiadiazinone dioxide derivative and a urea derivative.

It is known to use benzothiadiazinones and substituted ureaderivatives for controlling broadleaved and grassy weeds. However, an action of sufficiently broad spectrum is not always achieved.

We have now found that a composition of a benzothiadiazinone-(4)-2,2-dioxide of the formula where R denotes lower alkyl (isopropyl) or its salts, and a compound of the formula where R denotes 3,4-dichlorophenyl, 4-chlorophenyl,

4-fluorophenyl, 3-chloro-4-methylphenyl, 3-chloro-4- bromophenyl, 4-bromophenyl 3-chloro-4- methoxyphenyl 3-tert-butylcarbamoyloxyphenyl, 3- (N-vinyl-N-tert-butyl)-carbamoyloxyphenyl, 3-

isopropylcarbamoyloxyphenyl, 3-trifluoromethylphenyl, phenyl or N-2-benzothiazolyl, R denotes hydrogen, cyclohexenyl, cyclooctenyl,

or methyl, R denotes hydrogen, methyl, methoxyl, butyn-(1)-yl-3 or chloroformyl and X denotes oxygen or sulfur, has a good herbicidal action. Compositions having a ratio by weight of from 3 1 to l 3, especially 1 1, are preferred.

The new compounds may be used as herbicides in the form of solutions, emulsions, suspensions or dusts. The form of application depends entirely on the purpose for which the agents are to be used; in any case it should ensure a fine distribution of the active ingredient.

For the preparation of solutions to be sprayed direct, mineral oil fractions with medium to high boiling points, such as kerosene or diesel oil, coal-tar oils and oils of vegetable and animal origin, cyclic hydrocarbons, such as tetrahydronaphthalene, and alkylated naphthalenes are suitable.

Aqueous formulations may be prepared from emulsion concentrates, pastes or wettable powders by adding water. To prepare emulsions, the ingredients as such or dissolved in a solvent may be homogenized in water or organic solvents by means of wetting or dispersing agents. Concentrates which are suitable for dilution with water may be prepared from active ingredient, emulsifying or dispersing agent and possibly solvent.

The agents may be used as dispersion with dispersants, as emulsions with emulsifying agents or as oil dispersions with oils of various types. The oils may however also be added to the dispersions or emulsions direct.

Dusts may be prepared by mixing or grinding the active ingredients with a solid carrier. Compositions of the invention have a good action for instance on Alopecurus myosuroides, Apera spica venti, Poa spp., Echinochloa crus-galli, Setaria spp., Galium aparine, Matricaria spp., Sinapis arvensis, 'Stellaria media, Chrysanthemum segetum, and Xanthium spp. and may be used in many crop plants, e. g., cereals, Indian corn, sorgum, peanuts and soya beans.

Application rates are 1 to 4 kg'of active ingredient composition per hectare.

The use of the agents according to the invention is illustrated by the following examples.

The compositions of the invention are intended for postemergence use.

EXAMPLE 1 In the open, the plants Triticum aestivum, Hordeum vulgare, Secale cereale, Matricaria chamomilla, Galium aparine, Apera spica venti and Alopecurus myosuroides were treated at a growth height of 3 to 18 cm with the following composition and its individual components as oil dispersions with paraffin oil, dispersed in 500 liters of water.

I 3-isopropyl-2,l ,3-benzothiadiazinone-(4)-2,2- dioxide, 1.5 and 2.25 kg per hectare;

II N-p-chlorophenyl-N'-methyl-N-isobutynylurea,

0.75 and 2.25 kg per hectare;

I II 1.5 0.75 kg per hectare.

After approximately 14 days it was observed that the composition had the same good crop plant compatibility as the individual active ingredients, combined with a superior herbicidal action on the broadleaved and grassy weeds.

The results of the experiment are given in the following table:

0 no damage complete destruction EXAMPLE 2 In the open, the plants Triticum aestivum, Hordeum vulgare, Secale cereale, Matricaria chamomilla, Galium aparine, Apera spica venti and Alopecurus myosuroides 4 N -4-chlorophenyl-N '-methyl-N'-methoxyurea; N-3-chloro-4-methoxyphenyl-N,N--dimethylurea; N-3-trifluoromethylphenyl-N,N-dimethylurea; N-3-tert-butylcarbamoyloxyphenyl-N-methylurea;

N-3-chloro-4-methylphenyl-N N'-dimethylurea' were sprayed at a growth height of 2 to 17 cm with the following individual active ingredients and composition h 'buty thereof, each being dispersed in 500 liters of water per N'phenyl'N 'methoxyurea hectare N-3-chloro-4-methoxyphenyl-N-methyl-N- I 3-isopropyl-2,1,4-benzothiadiazinone-(4)-2,2- l0 methoxyurea; dioxide, 1 and 2 kg/ha; N-3-(N-vinyl-N-tert-butyl)-carbamoyloxyphenyl- II N-p-chlorophenyl-N'-methyl-N-isobutynylurea, 1 N,N'-dimethylurea; g 2 kg/ha; N-3-trifluoromethylphenyl-N-acetyloxymethyl-NN- an dimethylurea;

I+II1+1kg/ha. 15 I After days it was ascertained that the onset of ac- 9 P tion of the composition was more rapid than that of the Na4'dlchloroPhenyl'N'cyclohexenylN individual components, and that it had a superior overdlmethylurea all action. The results of the experiment are given be- N-3-trifluoromethylphenyl-N-cyclooctenyl-N'N'- low: dimethylurea;

I ll 1+ n kg/ha 1.0 2.0 1.0 2.0 1.0 1 0 Triticum aestivum O O 0 l5 0 Hordeum vulgane 0 0 0 l5 0 Secale cereale O O 0 2O 0 Matricana chamomilla 45 80 25 55 I00 Galium aparine 40 8O 45 90 Apera spica venti 55 I00 I00 Alopecurus myosumides 1O 20 50 80 90 0 no damage 100 complete destruction.

EXAMPLE 3 N-3-tert-butylcarbamoyloxyphenyl-N'-methyl-N'- In a greenhouse, the plants Triticum aestivum, H0rchloroformylurea; I I deum vulgare, Secale cereale, Chrysanthemum segetum, N'3'chloro'4'methylphenyl'N 'methyl'N Galium aparine, Apera spica venti, and Alopecurus myochloroformylurea' suroides were treated at a growth height of 3 to 19 cm 35 with the following amounts of the following active ingredients and composition thereof, each being dis- EXAMPLE 4 persed in 500 liters of water per hectare:

I 3-isopropyl-2,l ,3-benzothiadiazinone-( 4 )-2,2- dioxide, 1.5 and 3 kg/ha 40 In the open, the plants Triticum aestivum, Hordeum II N-( 2-benzothiazolyl )-N-methyl-N '-methylurea, 1.5 and 3 kg/ha; and

I II 1.5 1.5 kg per hectare.

After 10 to 14 days it was observed that the composition had a stronger action than II on Galium aparine and Chrysanthemum segetum and a stronger action than I on Apera spica venti and Alopecurus myosuroides, combined with good crop plant compatibility. The results of the experiment are given below:

vulgare, Galium aparine, Vicia spp., Apera spica venti and Alopecurus myosuroides were treated at a growth height of 3 to 20 cm with the following amounts of the following individual active ingredients and compositions thereof, each being dispersed in 500 liters of water per hectare:

I 3-isopropyl-2,l ,3-benzothiadiazinone-(4 )-2 ,2- dioxide, 1, 2 and 3 kg per hectare;

II N-cyclohexenyl-N-3-chloro-4-methylphenyl- N,N-dimethylurea, 1 and 3 kg per hectare;

0 no damage 100 complete destruction The action of the following compositions corresponds to that of the above composition:

3-isopropyl-2,1 ,3-benzothiadiazinone-(4)-2,2-

dioxide N-3-chloro-4-bromophenyl-N-methyl-N- methoxyurea;

III N-3-chloro-4-methoxyphenyl-N'-methyl-N methoxyurea, 2 and 3 kg per hectare;

IV N-3-chlor0-4-methylphenyl-N,N-dimethylurea, 1 and 2 kg per hectare;

V N-(2-benzothiazolyl)-N-methyl-N-methylurea, 2 and 3 kg per hectare;

I II 2 1 kg per hectare;

I Ill 1 2 kg per hectare; I IV 1 1 kg per hectare; I +V l 2 kg per hectare.

After 2 to 3 weeks it was ascertained that the compositions, compared with the individual active ingredi- 5 ents, had a superior herbicidal action combined with a more favorable crop plant compatibility.

The results of the experiment are given in the follow- 6 sodium salt of 3-sec-butyl-2,1,3-benzothiadiazinone- (4)-2,2-dioxide -l-. 1 3 N-( 4-chlorophenyl )-N '-methyl-N '-butynl -yl-3- urea; Y

N-phenyl-N-methoxy-N-methylurea; N-(4-chlorophenyl)-N'-methoxy-N-'-methylurea;

N-( 3 ,4-dichlorophenyl)-N '-methoxy-N'-.methylurea;

ing table: N-(3-trifluoromethylphen l)-N,N'-dimethylurea;

y 10 N-( 3-chloro-4-bromophenyl )-N -methxy-N methylurea; 1 a m N-(3-chloro-4-methoxyphenyl)-N,N-dimethylurea; kg/htl l 2 3 2 3 1 I2 N-(3-chloro-4-meth0x henyl)-N-cyclohex+-l-enyl- YP N N-dimethylurea' T txcum aestzvum O 0 0 O ,25 0 l0 0 2O li tirdeum v'ul are 0 0 0 5 5 3o 0 5 20 N-(3-chloro-4-methoxyphenyl)-N-cyclohex-l-enyl- Galium aparine 40 75 95 IO 25 25 35 35 q Vim spp. 10 35 25 60 50 20 methylutea l Apem Spica venti 20 so 35 60 95 65 90 65 95 l l i fi y -g y y y -(muorome- Alopecur ts t y p y r a; myosm'des 1O 20 30 55 90 60 85 6o 95 N'-(3-trifluoromethylphenyl)-N-cyclooctenyl-N',N-

v 1+11 1+111 1+1v 1+v 20 dimethylurea; kg/ha 2 3 2 +1 1+ 2 N-(3,4-dichlorophenyl)-N-cyclohex-1-enyl-N',N'- Triticum aestivum 0 25 0 0 0 0 dlmethylureaflvrfieum vulpare 5 20 5 5 III N-(3-chloro-4-methylphenyl)-NZN'- sl zgtgrzzparme $8 Q1380 dimethylurea, 1.5 and 3 kg/ha; Apera spica verm' 70 100 100 95 100 100 25 IV N-(2-benzothiazolyl)-N-methyl-N'-methylurea, 2 5 and 4 kg/ha' myosuroides 7O 95 -95 '90 95 100 o no damage V N-(3-chloro-4-methoxyphenyl)-N',N lOO =complete destruction. dimethylurea, 3 and 4 kg/ha;

I-+ II 2.0 1.0 kg/ha; 1 1+111 1.5 1.5 kg/ha; The action of the following compositions corre g/ sponds to that of those above: I V 1- 3-0 g/hadimethylamine salt of 3-isopropyl-2,l ,3- The results given in the following table were obtained benzothiadiazinome-(4)-2,2-dioxide, or after 3 to 4 weeks.

1 11 111 kg/ha 1 1 5 2 3 4 1 3 1.5

Triricum aestivum 0 O 0 O 0 0 2O 5 25 S260]? cereale 0 O 0 O O 0 3O 5 3O Galium aparine 35 50 7O 40 lOO I0 55 20 Alopecurus myosuruide: 5 l0 I5 25 35 90 I00 [V v 1+ 11 1+ 111 kg/ha 2.5 4 3 4 2 1 1.5 1.5

Triticum aeslivum 0 30 0 l0 0 5 Secale cereale 5 30 5 l0 0 5 Galium aparine 3O 50 45 9O 95 Alopecums myosuroidex 100 90 1 +1v 1 v kg/ha 1.5 +1.5 1+ 3 Tn'licum aestivum 0 O Secale cereale 5 5 Galium aparine lOO 9S Alopecurus myosuroides I00 0 no damage I00 complete destruction.

EXAMPLE 5 EXAMPLE 6 In a greenhouse, the plants Triticum aestivum, Secale cereale, Galium aparine and Alopecurus myosuroides were treated shortly before or during emergence with the following amounts of the following individual active ingredients and compositions thereof in the form of granules:

I 3-isopropyl-2,l ,3-benzothiadiazinone-(4)-2,2- dioxide, 1, 1.5, 2, 3 and 4 kg/ha;

II N-(4-chlorophenyl)-N'-methy1-N '-butyn-l-yl-3- urea, 1 and 3 kg/ha;

3-isopropyl-2,l ,3-

0.5, 2 and 3 ll 3-sec-butyl-2,l ,3-benzothiadiazinone-(4)-2,2- dioxide, 1, 1.5 and 2 kg/ha;

Ill N-3 ,4-dichlrophenyl-N -methoxy-N methylurea; 0.5 and 1.5 kg/ha;

1 claim:

1. A herbicide composition comprising a herbicidally effective amount of a mixture of IV y P y Z imethylurea; 1 a. a member selected from the group consisting of 3- and 2 kg/ha; isopr0pyl-2,l,3-benzothiadiazinone-(4)-2,2-

p y y dioxide, the sodium salt thereof and the dimethyldlmethylureat 1 and 3 kg/ha; amine salt thereof; and

VI N-4-bromophenyl-N'-methyl-N-methoxyurea, 1 5 and 2 kg/ha; b. a member selected from the group consisting of N- I v 2 1 kg/ha; 3-chloro-4-methoxyphenyl-N-methyl-N- I V] 5 k /h methoxyurea, N-3-chloro-4-methylphenyl-N,N'- II [II 1 05 k /h dimethylurea, N-(2-benzothiazolyl)-N-methyl-N'- II IV 1 l kg/ha. methylurea, N4-chlorophenyl-N-methyl-N'-butyn- After 2w 3 weeks it was ascertained that the compo- 15 -y and -h -4-m th0Xyphenylsitions had a better herbicidal action than the individ- N',N'-dimethylurea ual active ingredients, combined with superior crop in a weight ratio of (a) to (b) in the range of 3:1 to 1:3. plant compatibility.

The results of this experiment are given in the following table:

l n III IV kg/ha 05 2 3 1 1.5 2 0.5 1.5 l 2 Zea mays O 0 0 O O 5 0 2O 0 10 Pm: annua 5 20 i0 i5 20 60 95 70 95 Echirwchloa crus-galli 5 15 25 l0 I5 25 55 85 6O 90 Cyperus exculenlus 3O 85 90 70 95 20 25 45 Galium apun'ne 30 75 100 70 so 25 e5 20 40 V VI I v I v1 n+1" ll+lV kg/ha l 3 1.5 2 2 l 0.5+1.5 1+1 Zea mays 0 l5 0 l0 0 0 0 0 Pua annua 60 W0 85 95 90 90 90 Echinochlaa crus galli mo 95 95 I00 85 Cypems esculentus I5 45 40 55 100 85 85 85 Galium apan'ne l0 40 3O 45 I00 100 UNITED STATES PATENT AND TRADEMARK OFFICE CERTIFICATE OF CORRECTION PATENT NO. 3,912,489 DATED October 14, 1975 |NVENTOR(S) FISCHER It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:

Column 5, the heading of the table, add --II-- above "1'' (second occurence) Column 7, the heading on the top of the 2nd table, delete "1VI" and substitute --l+VI-- Column 7, the heading on the top of the 2nd table, delete "+0.5" and substitute --l+O.5--

Signed and Sealed this Fourteenth D3) of September 1976 [SEAL] A ttest:

RUTH C. MASON C. MARSHALL DANN r-trrzstr'ng Officer Commissioner nflarenls and Trademarks 

1. A HERBICIDE COMPOSITION COMPRISING A HERBICIDALLY EFFECTIVE AMOUNT OF A MIXTURE OF A. A MEMBER SELECTED FROM THE GROUP CONSISTING OF 3-ISOPROPYL-2,1,3-BENZOTHIADIAZINONE-(4)2,2-DIOXIDE THE SODIUM SALT THEREOF AND THE DIMETYLAMINE SALT THEREOF AND B A MEMBER SELECTED FROM THE GROUP CONSISTING OF N-3CHLORO-4-METHOXYPHENYL-N''-METHYL-N'' METHOXYUREA, N-3-CHLORO-4-METHYLPHENYL-N''N''-DIMETHYLUREA N-(2BENZOTHIAZOLY) N-METHYL N''METHYLUREA N4-CHLOROPHENYL-N-METHYL-N''BUTYN 1-YL-3-UREA AND N-3-CHLORO-4METHOXYPHENYL-N''N''-DIMETHYLUREA IN A WEIGHT RATIO OF (A) TO (B) IN THE RANGE OF 3:1 TO 1:3 